1. Congratulations! We know you've entered the contest over a dozen times. How are you feeling now?
Yes, I’ve probably entered 20 times since I got to the island 24 years ago! I’ve always loved seeing the posters around the island—Thomas Hart Benton and Allen Whiting and all the others—and I’m psyched to hang beside them in the hall. There’s such a beautiful sense of history and I’ve always wanted to be a part of that. I love the idea of families wearing my shirt of my design. It’s just so fun. I’m so happy I won! Thank you!

2. Tell us a little more about yourself!
I am a full-time artist in Oak Bluffs, where I live with my two cats Winslow and Theo and my dog Happy. My girlfriend Lauren has a house nine minutes down the road with her two kids Marina and Nico. When I’m not painting, I am going to the beaches, playing with Lauren and Marina and Nico, going on little adventures—taking advantage of all the amazing things the island has to offer, including the Ag Fair. I absolutely love the island and all the people and everything about it. It’s a dreamland. Of course, life has cloudy days but the majority of the time, the sun's out! You can see more of my work at traegerdipietro.com, the Field Gallery, and North Water Street Gallery.

3. What inspired your design this year?
Last year at the Fair, I saw a really sweet couple standing by the fence, so that was in my head. They were very casual and relaxed, enjoying the Fair. Then I wanted to incorporate Lauren and the children—that’s where the creative license took place. I wanted it to be diverse and uplifting with glitter and sparkles.

4. What is your favorite Fair memory?
My favorite Fair memory is walking into the Fair and seeing Marina and Nico on the Ferris Wheel waving down at me. They were so happy and so excited to be so high up. It stopped at the exact moment so when I walked in, they were at the top and I could see how high up they were. We all were so happy!

5. This year is our 162nd Agricultural Fair! What do you love most about the Fair?
I think I love the energy the best. I feel like we’re surrounded by little dreams and imaginations that the kids have before they go…the excitement of going on the rides and eating cotton candy. The kids are so excited to get to go and do these amazing things that are put on by everyone working so hard. The Fair is never-ending, it’s timeless. It doesn’t matter how old you are—it brings you back to those moments.